WO2007116948A1

WO2007116948A1 - Plant protection method

Info

Publication number: WO2007116948A1
Application number: PCT/JP2007/057696
Authority: WO
Inventors: Norihisa Sakamoto; Masato Konobe
Original assignee: Sumitomo Chemical Company, Limited
Priority date: 2006-04-03
Filing date: 2007-03-30
Publication date: 2007-10-18

Abstract

A plant can be protected from the pest damage by applying an effective amount of an (N'-methyl)benzoylurea compound represented by the formula (I) or a salt thereof to a root, a seed or a rhizosphere of the plant. (I) wherein X, R1, R2, R3 and m are as defined in the description.

Description

1

Descriptions Plant protection methods Technical field

The present invention relates to a plant protection method, and more particularly to a plant protection method from harm by pests. Background art

GB 1 3 2 4 2 9 3, U.S. Pat.No. 4 2 4 3 6 8 0, WO 9 7/4 5 0 1 7 pamphlet, WO 9 9 Z 1 6 3 1 6 pamphlet , US Patent No. 5 8 6 2 2 1 and pamphlet of International Publication No. 9 8/1 9 5 4 3, N, 1-ethyl benzoylurea compounds having an ethylated N, position are described . Disclosure of the invention

An object of the present invention is to provide a method for protecting plants from harm by pests. As a result of intensive studies to find a new plant protection method, the present inventors have determined that an effective amount of an N′-ethylbenzoylurea compound represented by the following formula (I) or a salt thereof is the root or seed of a plant, or a plant It was found that by applying to the root zone of the plant, the plant can be protected from harm by pests, and the present invention has been reached.

That is, the present invention is as follows.

1. Formula (I)

[Where,

X and Y each represents a fluorine atom or a chlorine atom,

R ¹ is a hydrogen atom or a C 1 alkyl group optionally substituted with a halogen atom, C C 2—C 6 alkenyl, C 2—C 6 alkynyl, C6—C 14 aryl, C7—C 11 aralkyl, C2—C 6 alkoxyalkyl, C 7— C 14 aryloxyalkyl group, C3—C6N, N —di (alkyl) aminoalkyl group, C 2—C 6 alkylthioalkyl group, C2—C 6 alkylsulfinylalkyl group, C 2—C 6 alkylsulfonyl alkyl group Group, C3-C9 alkoxyalkoxyalkyl group, C2-C6 alkoxycarbonyl group, C8-C12 aralkyloxycarbonyl group, N, N-di (C1 C6 alkyl) Carpamoyl group, C 2-C 6 alkylcarbonyl group optionally substituted with a halogen atom, formyl group, C 1 -C 5 alkylsulfonyl group optionally substituted with a halogen atom or C 6- C 10 aryl Represents a rusulfonyl group,

R ² represents a halogen atom or a C 1 -C 4 alkyl group which may be substituted with a halogen atom,

R ³ is a halogen atom, an optionally substituted C 1 -C 4 alkyl group, an optionally substituted C 1 -C 4 alkoxy group, an optionally substituted C 2- A C6-alkoxyalkoxy group, a C2-C4 alkenyloxy group optionally substituted with a halogen atom or a C2-C4 alkynyloxy group optionally substituted with a halogen atom,

m represents one of integers from 0 to 4. ]

(Ν '-ethyl) benzoylurea compound (hereinafter sometimes referred to as the present compound) or a salt thereof is applied to the root or seed of the plant, or the rhizosphere of the plant. A method for protecting a plant from harm by a pest having a process. 2. In the formula (I), R ¹ is a hydrogen atom, R ³ is a C 1 -C 4 alkoxy group which may be substituted with a halogen atom or a halogen atom, or a C 1 which may be substituted with a halogen atom A C4 alkyl group having m or 0 or 1 and applying an effective amount of (Ν'-ethyl) benzoylurea compound or a salt thereof to the root or seed of a plant or the rhizosphere of a plant 1. Methods for protecting plants from harm by the described pests.

3. The plant protection method according to 1. or 2., wherein the root or seed of the plant or the root zone of the plant is the root zone of the plant.

4. The plant protection method according to 3., wherein the root zone of the plant is a soil on which the plant grows.

5. Formula (I)

[Where,

X and Y each represents a fluorine atom or a chlorine atom,

R ¹ is a hydrogen atom, a C 1—C 6 alkyl group optionally substituted with a halogen atom, a C 2—C 6 alkenyl group optionally substituted with a halogen atom, a C 2—C 6 alkynyl group, C 6 —C14 aryl group, C 7—C 11 aralkyl group, C2—C6 alkoxyalkyl group, C 7—C14 aryloxyalkyl group, C3—C6N, Ν- (alkyl) aminoalkyl group, C 2— C6 alkylthioalkyl group, C2-C6 alkylsulfinylalkyl group, C2-C6 alkylsulfonylalkyl group, C3-C9 alkoxyalkoxyalkyl group, C2-C6 alkoxycarbonyl group, C8-C 12 aralkyloxycarbonyl group, Ν, Ν-di (C1-C6 alkyl) force rubamoyl group, C2-C6 alkylcarbonyl group optionally substituted with halogen atom, formyl group, halogen C optionally substituted by atoms 1 shows an C 5 alkylsulfonyl group or a C 6- C 10 § reel sulfonyl group, R ² represents a halogen atom or a C port Gen C 1 one C 4 alkyl Le optionally substituted with atoms,

R ³ is a halogen atom, a C 1 -C 4 alkyl group which may be substituted with a halogen atom, a C 1 -C 4 alkoxy group which may be substituted with a halogen atom, or a C 2—optionally substituted with a halogen atom. A C6 alkoxyalkoxy group, a C2-C4 alkenyloxy group optionally substituted with a halogen atom or a C2-C4 alkynyloxy group optionally substituted with a halogen atom;

m represents one of integers from 0 to 4. ]

(Ν'-ethyl) A plant protective agent against harm by pests containing a benzoylurea compound or a salt thereof and an inert carrier.

6. In formula (I), R ¹ is a hydrogen atom, R ³ is a halogen atom, a C 1 -C 4 alkoxy group that may be substituted with a halogen atom, or a C 1 that is optionally substituted with a halogen atom 1 C 4 alkyl group: ϋ, m is 0 or 1 (N, —ethyl) Contains a benzoylurea compound or a salt thereof and an inert carrier 5. Plant protection from harm by harmful organisms according to 5. Agent. 7. The plant protective agent according to 5. or 6, which is used for treatment of the plant rhizosphere.

8. The plant protective agent according to 5. or 6, which is used for treating soil in which plants grow.

9. (Ν '-ethyl) benzoyl urea compound or its salt for application to plant root or seed or plant rhizosphere to protect plant from harm by pests Use of. In the present invention, represented by R ¹ of the present compound,

Examples of the C 1 -C 6 alkyl group which may be substituted with a halogen atom include a methyl group, a chloromethyl group, a difluoromethyl group, a trichloromethyl group, an ethyl group, a 2-promoethyl group, and 2, 2, 2-trifluor. Oloethyl group, propyl group, 3, 3, 3-trifluoropropyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, 4, 4, 4 trifluorobutyl group Pentyl group, isopentyl group, neopentyl group, 5,5,5-trifluoropentyl group, hexyl group and 6,6,6-trifluorohexyl group,

Examples of the C 2 -C 6 alkenyl group which may be substituted with a halogen atom include a vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 2-butenyl group, and isobutenyl. Group and 3, 3-dichloro-2-propenyl group, and C 2 -C 6 alkynyl group includes, for example, ethynyl group, 2-propier group and 1-propynyl group,

Examples of the C 6 -C 14 aryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, and a biphenylyl group,

Examples of the C7-C11 aralkyl group include a benzyl group and a phenethyl group,

Examples of the C 2 -C 6 alkoxyalkyl group include a methoxymethyl group, an ethoxymethyl group, a 1-propoxymethyl group, a 2-methoxyethyl group, a 2-methoxy group, a 3-methoxypropyl group and a 3-ethoxypropyl group. Named,

Examples of the C 7- C 14 aryloxyalkyl group include a phenoxymethyl group and a 2-phenoxychetyl group,

Examples of the C3-C6N, N-di (alkyl) aminoalkyl group include a dimethylaminomethyl group, 2- (dimethylamino) ethyl group, jetylaminomethyl group, and 2- (jetylamino) ethyl group,

Examples of the C 2 -C 6 alkylthioalkyl group include a methylthiomethyl group, A ruthiomethyl group, a 2- (methylthio) ethyl group and a 2- (ethylthio) ethyl group,

Examples of the C 2 -C 6 alkylsulfinylalkyl group include a methylsulfinylmethyl group, an ethylsulfinylmethyl group, a 2- (methylsulfiel) ethyl group, and a 2- (ethylsulfinyl) ethyl group,

Examples of the C 2 -C 6 alkylsulfonylalkyl group include a methylsulfonylmethyl group, an ethylsulfonylmethyl group, a 2- (methylsulfonyl) ethyl group, and a 2- (ethylsulfonyl) ethyl group,

Examples of the C 3 -C 9 alkoxyalkoxyalkyl group include (2-methoxyethoxy) methyl group,

Examples of the C 2 -C 6 alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, an isopropoxy group, a normal butoxycarbonyl group, and a tert-butoxycarbonyl group.

Examples of the C 8 -C 12 aralkyloxycarbonyl group include a benzyloxycarbonyl group,

N, N-di (〇 1-6. Alkyl) Examples of strong rubermoyl groups include dimethylcarbamoyl and jetylcarbamoyl.

Examples of the C 2 -C 6 alkylcarbonyl group which may be substituted with a halogen atom include a acetyl group, a propionyl group, a trifluoroacetyl group and a chloroacetyl group,

Examples of the C 1 -C 5 alkylsulfonyl group optionally substituted with a halogen atom include a methylsulfonyl group, an ethanesulfonyl group, and a trifluoromethylsulfonyl group,

Examples of the C 6 -C 10 arylaryl group include a benzenesulfonyl group and a toluenesulfonyl group,

Represented by R ^2,

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Examples of the C 1 .1 C 4 alkyl group optionally substituted with a halogen atom include a methyl group, a chloromethyl group, a difluoromethyl group, a trichloromethyl group, a trifluoromethyl group, an ethyl group, a 2-bromoethyl group, 2, 2, 2—Trifluoroec Group, pentafluoroethyl group, propyl group, 3, 3, 3-trifluoropropyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group and 4, 4, 4 One trifluorobutyl group,

Indicated by R ³ ,

Examples of the C 1 -C 4 alkyl group which may be substituted with a halogen atom include a methyl group, a chloromethyl group, a difluoromethyl group, a trichloromethyl group, a trifluoromethyl group, an ethyl group, a 2-bromoethyl group, 2, 2, 2-trifluoro group, pentafluoroethyl group, propyl group, 3, 3, 3-trifluoropropyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group and 4, 4, 4 trifluorobutyl group,

Examples of the C 1 -C 4 alkoxy group which may be substituted with a halogen atom include a methoxy group, an ethoxy group, a 1-propyloxy group, an isopropoxy group, a tert-butoxy group, a difluoromethoxy group, and a trifluoro group. Methoxy group, 2, 2, 2-trifluorofluoro group, 1, 1, 2, 2, 2-pentafluoroethoxy group, 1, 1, 2, 2-tetrafluoroethoxy group, 1, 1, 2 , 2, 3, 3, 3—heptofluor 1-propoxy group and 1,1,2,3,3,3-hexafluoro-1-propoxy group,

Examples of the C 2 -C 6 alkoxyalkoxy group optionally substituted with a halogen atom include 2-trifluoromethoxy-1,1,2-trifluoroethoxy group,

Examples of the C 2 -C 4 alkenyloxy group optionally substituted with a halogen atom include a 2-propenyloxy group and a 3,3-dichloro-2-propenyloxy group,

Examples of the C 2 -C 4 alkynyloxy group which may be substituted with a halogen atom include a 2-propynyloxy group. This compound can form an acid.addition salt in which a basic group such as a dialkylamino group in a substituent in the molecule can be agrochemically acceptable with an inorganic acid or an organic acid. Examples of the inorganic acid addition salt of the compound include hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, and perchloric acid, and examples of the organic acid addition salt of the compound include Formic acid, vinegar Examples thereof include salts with acid, propionic acid, succinic acid, succinic acid, benzoic acid, p-toluenesulfonic acid, methanesulfonic acid, and trifluoroacetic acid. Next, the synthesis method of this compound is shown.

This compound can be produced, for example, by the following (Synthesis Method 1) to (Synthesis Method 4).

(Synthesis Method 1)

Of this compound, the formula (1— 1)

[Wherein, X, Y, R ² , R ³ and m represent the same meaning as described above. ]

The compound represented by the formula (I I)

[Wherein, X and Y represent the same meaning as described above. ]

A compound of formula (III)

[Wherein R ² , R ³ and m represent the same meaning as described above. ]

It can manufacture by making the compound shown by react.

The reaction is usually performed in a solvent.

Examples of the solvent used in the reaction include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene, and xylene, aliphatic hydrocarbons such as hexane and heptane, jetyl ether, tetrahydrofuran, 1 , 4-dioxane, 1,2-dimethoxyethane, ethers such as 1,2-jetoxetane, halogenated hydrocarbons such as chloroform, benzene, dichlorobenzene, acetate Nitriles such as nitrile, aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone, dimethylsulfoxide, water and the like A mixture may be mentioned.

The amount of the compound represented by the formula (III) used in the reaction is usually 0.5 to 2 mol relative to 1 mol of the compound represented by the formula (II).

The reaction temperature is usually in the range of 78 to 15 Ot :, and the reaction time is usually in the range of 0.1 to 100 hours.

After completion of the reaction, for example, the reaction mixture is poured into water, extracted with an organic solvent, and then subjected to post-treatment operations such as drying and concentration of the organic layer. Can be isolated. The isolated compound represented by the formula (I-11) can be further purified by recrystallization, column chromatography or the like.

(Synthesis Method 2)

Among the compounds, the formula (I 1 2)

[Wherein, X, Y, R ² , R ³ and m are as defined above, R ¹ — ¹ is a C 1 C 6 alkyl group optionally substituted with a halogen atom, substituted with a halogen atom C 2—C 6 alkenyl group, C 2—C 6 alkynyl group, C6—C 14 aryl group, C7—C 11 aralkyl group, C 2—C 6 alkoxyalkyl group, C 7— C14 aryloxyalkyl group, C3-C6N, N-di (alkyl) aminoalkyl group, C2-C6 alkylthioalkyl group, C2-C6 alkylsulfurylalkyl group, C2-C6 alkyl Represents a sulfonylalkyl group or a C 3 -C 9 alkoxyalkoxyalkyl group; ]

The compound represented by formula (IV) (IV)

Wherein, X, Y and R ¹ one ¹ are as defined above. ] Can be produced by reacting the compound represented by formula (III) with the compound represented by formula (III).

The reaction is usually performed in a solvent in the presence of a base.

Examples of the solvent used in the reaction include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene, and xylene, aliphatic hydrocarbons such as hexane and heptane, jetyl ether, tetrahydrofuran, 1 , 4-dioxane, 1,2-dimethoxyethane, ethers such as 1,2-diethoxyethane, etc., halogenated hydrocarbons such as chloroform, benzene and dichlorobenzene, nitriles such as acetonitrile, Aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone, dimethyl sulfoxide, water, and mixtures thereof. Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, hydrogenated hydroxide of alkaline metal or alkaline metal such as sodium hydroxide, lithium hydroxide, calcium hydroxide, and the like. Alkali metals such as calcium or alkali earth metal hydrides, alkali metals such as sodium carbonate or potassium carbonate, or alkaline earth metal carbonates, sodium ethylate, sodium methylate, etc. And organic bases such as organic lithium such as normal butyl lithium and lithium diisopropylamide and triethylamine, pyridine, 1,8-diazabicyclo [5,4,0] undecene (hereinafter abbreviated as DBU).

The amount of the reagent used in the reaction can be used in an excess amount when using a reagent that is liquid under the reaction conditions, but usually the formula (IV) is added to 1 mol of the compound represented by formula (IV). The compound represented by III) is 1 to 4 moles, and the base is 1 to 4 moles.

The reaction temperature is usually in the range of 1 78 to 15 50, and the reaction time is usually in the range of 0.1 to 20 hours.

After completion of the reaction, for example, the reaction mixture is poured into water, extracted with an organic solvent, and then subjected to post-treatment operations such as drying and concentrating the organic layer, whereby a compound represented by the formula (I-12) is obtained. Can be isolated. The isolated compound represented by the formula (1-2) can be further purified by recrystallization, column chromatography or the like.

(Synthesis Method 3) Among these compounds, the formula (1-3)

( ³ )

Wherein, XYR ² R ³ and m are as defined above, R ¹ - ² are halogen atoms which may be substituted with child C 1 one C 6 alkyl group, it may be substituted with a halogen atom C.2—C 6 alkenyl group, C 2—C 6 alkynyl group, C7—C 11 aralkyl group, C 2—C 6 alkoxyalkyl group, C 7—C 14 aralkyl group, C3— C6N, N-di (alkyl) aminoalkyl group, C2-C6 alkylthioalkyl group, C2-C6 alkylsulfinylalkyl group, C2-C6 alkylsulfonylalkyl group, C3-C9 alkoxyalkoxyalkyl group C 2—C 6 alkoxycarbonyl group, C 8—C 12 aralkyloxycarbonyl group, N, N—di (CI—C6 alkyl) group, rubamoyl group, optionally substituted by halogen atom C 2 — Substitute with C 6 alkyl carbonyl group, formyl group, halogen atom Represents a C1-C5 alkylsulfonyl group or a C6-C10 arylsulfonyl group which may be substituted. ]

A compound represented by formula (I-1) and a compound represented by formula (V)

Li I _R i-2 (V)

[In the formula, R ¹ one ² are as defined above, L ¹ is a halogen atom (e.g., chlorine atom and bromine atom), methanesulfonyl O alkoxy group, benzenesulfonyl O alkoxy group, toluene sulfonyl O alkoxy group, Represents a methoxysulfonyloxy group or an ethoxysulfonyloxy group. ]

Can be produced by reacting with a compound represented by the above in the presence of a base.

The reaction is usually performed in a solvent in the presence of a base.

Examples of the solvent used in the reaction include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene and xylene, aliphatic hydrocarbons such as hexane and heptane, jetyl ether, tetrahydrofuran, 1 4-1 ethers, ethers such as 1,2-dimethoxyethane, 1,2-diethoxyethane, halogenated hydrocarbons such as chloroform, chlorobenzene, dichlorobenzene, nitriles such as acetonitrile, NN-dimethylformamide , N, N-dimethyla Examples thereof include aprotic polar solvents such as cetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone and dimethyl sulfoxide, water, and mixtures thereof.

Examples of the base used in the reaction include alkali metal or alkaline earth metal hydroxides such as sodium hydroxide, hydroxy hydroxide, calcium hydroxide, and alkali such as sodium hydride, potassium hydride, and calcium hydride. Metal or alkali earth metal hydride, alkali metal such as sodium carbonate or potassium carbonate or carbonate of alkaline earth metal, sodium metallate, alkali metal alcoholate such as sodium methylate, Examples include organic lithium such as normal butyl lithium and lithium diisopropylamide, and organic bases such as triethylamine, pyridine and DBU.

The amount of the reagent used in the reaction can be used in an excess amount when using a reagent that is liquid under the reaction conditions, but is usually based on 1 mole of the compound represented by the formula (I 1 1). The compound represented by the formula (V) is 1 to 4 mol, and the base is 1 to 4 mol.

The reaction temperature is usually in the range of −78 to 1550, and the reaction time is usually in the range of 0.1 to 100 hours.

After completion of the reaction, for example, the reaction mixture is poured into water, extracted with an organic solvent, and then subjected to post-treatment operations such as drying and concentration of the organic layer, whereby the compound represented by the formula (1-3) is obtained. Product can be isolated. The isolated compound represented by the formula (1-3) can be further purified by recrystallization, column chromatography or the like.

(Synthesis Method 4)

Among the compounds (I), the compound of formula (I

[Wherein, X, Y, R ² , R ³ , R ¹ — ¹ and m represent the same meaning as described above. ] The compound represented by the formula (VI)

[Wherein, X and Y represent the same meaning as described above, and L ² represents a halogen atom (for example, a chlorine atom, a bromine atom and an iodine atom). ]

And a compound of formula (VI I)

[Wherein, R Bok ^1, R ^2, R ³ and m are as defined above. ]

It can manufacture by making the compound shown by react.

The reaction is usually performed in a solvent in the presence of a base.

Solvents used in the reaction include, for example, ketones such as acetone and methyl edyl ketone, aromatic hydrocarbons such as benzene, toluene and xylene, aliphatic hydrocarbons such as hexane and heptane, jetyl ether, tetrahydrofuran, 1 , 4-dioxane, 1,2-dimethoxyethane, ethers such as 1,2-diethoxyethane, halogenated hydrocarbons such as chloroform, benzene, dichlorobenzene, nitriles such as acetonitrile, N , N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone, dimethylsulfoxide, and other aprotic polar solvents, water, and mixtures thereof.

Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, hydrogenated hydroxide of alkaline metal or alkaline metal such as sodium hydroxide, lithium hydroxide, calcium hydroxide, and the like. Alkali metals such as calcium or alkali earth metal hydrides, alkali metals such as sodium carbonate or potassium carbonate, or alkaline earth metal carbonates, sodium ethylate, sodium methylate, etc. Organic lithium such as normal butyl lithium and lithium diisopropylamide, and organic bases such as triethylamine, diisopropylethylamine, pyridine and DBU.

The amount of the reagent used in the reaction may be an excess of each when a reagent that is liquid under the reaction conditions is used, but usually the compound 1 represented by the formula (VI I) The proportion of the compound represented by the formula (VI) is 1 to 4 mol and the base is 1 to 4 mol with respect to mol.

The reaction temperature is usually in the range of −78 to 180 ° C., and the reaction time is usually in the range of 0.1 to 200 hours.

After completion of the reaction, for example, the reaction mixture is poured into water, extracted with an organic solvent, and then subjected to post-treatment operations such as drying and concentration of the organic layer, whereby the compound represented by the formula (1-2) is obtained. Can be isolated. The isolated compound represented by the formula (1-2) can be further purified by recrystallization, column chromatography or the like. Next, a reference synthesis method of a synthetic intermediate of this compound will be shown.

(Reference Synthesis Method 1)

The compound represented by the formula (IV) is represented by the formula (VI II)

[Wherein, X, Y and R ¹ represent the same meaning as described above. ]

It can be produced by reacting a minylating agent.

The reaction is usually performed in a solvent in the presence of a base.

Examples of the solvent used in the reaction include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene and xylene, aliphatic hydrocarbons such as hexane and heptane, jetyl ether, tetrahydrofuran, 1 , 4-dioxane, ethers such as 1,2-dimethoxyethane, 1,2-diethoxyethane, halogenated hydrocarbons such as chloroform, chlorobenzene, dichlorobenzene, nitriles such as acetonitrile, N, N Examples include aprotic polar solvents such as —dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone, dimethylsulfoxide, water, and mixtures thereof.

Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, hydrogenated hydroxide of alkaline metal or alkaline metal such as sodium hydroxide, lithium hydroxide, calcium hydroxide, and the like. Alkali metals such as calcium or alkali earth metal hydrides, alkali metals such as sodium carbonate and potassium carbonate Examples include alkaline earth metal carbonates, alkali metal alcoholates such as sodium edilate and sodium methylate, organic lithiums such as normal butyl lithium and lithium diisopropylamide, and organic bases such as triethylamine, pyridine and DBU. .

Examples of the trialkylchlorosilane compound used in the reaction include trimethyl silane and triethyl silane.

Examples of the chlorocarbonylating agent used in the reaction include phosgene, trimethyl oral formate, bis (trichloromethyl) carbonate and the like. The amount of the reagent used in the reaction is usually 1 to 4 moles of the trialkylchlorosilane compound and 1 to 4 moles of the carbonyl carbonylating agent with respect to 1 mole of the compound represented by the formula (VI II). The base is usually in a ratio of 1 to 4 moles.

The reaction temperature is usually in the range of 78 to 150 ° C, and the reaction time is usually in the range of 0.1 to 200 hours.

After completion of the reaction, the compound represented by the formula (IV) can be isolated by performing post-treatment operations such as concentrating the reaction mixture as it is. The isolated compound represented by the formula (IV) can be used in the next step without purification.

(Reference Synthesis Method 2)

The compound represented by the formula (VI I) is represented by the formula (IX)

(ix)

[Wherein R ² , R ³ and m represent the same meaning as described above. ]

And a compound of formula (X)

H ₂ N-R ^1-1 (X)

[Wherein, R ¹ represents the same meaning as described above. ]

It can manufacture by making the compound shown by react.

The reaction is usually performed in a solvent in the presence of a base.

Examples of the solvent used in the reaction include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene and xylene, aliphatic hydrocarbons such as hexane and heptane, jetyl ether, tetrahydrofuran, 1 , 4—Zoki Sun, ethers such as 1,2-dimethoxyethane, 1,2-diethoxyethane, halogenated hydrocarbons such as chloroform, chlorobenzene, dichlorobenzene, nitrile such as acetonitrile, N, N-dimethylformamide, Aprotic polar solvents such as N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolinone, dimethyl sulfoxide, water, and mixtures thereof.

Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, hydrogenated hydroxide of alkaline metal or alkaline metal such as sodium hydroxide, lithium hydroxide, calcium hydroxide, and the like. Alkali metal such as calcium or alkali earth metal hydride, alkali metal such as sodium carbonate or potassium carbonate or carbonate of alkaline earth metal, sodium ethylate, sodium methylate, etc. Examples include organic lithium such as alcoholate, normal butyl lithium, lithium diisopropylamide, and organic bases such as triethylamine and DBU. Alternatively, an excess amount of (X) can be used as the base.

The amount of the reagent used in the reaction is 1 to 6 moles of the compound represented by formula (X) and 1 to 6 moles of the base, based on 1 mole of the compound represented by formula (IX). The

After completion of the reaction, for example, the compound represented by the formula (VI I) is isolated by performing post-treatment operations such as pouring the reaction mixture into water, extracting with an organic solvent, and then drying and concentrating the organic layer. can do. The isolated compound represented by the formula (VI I) can be further purified by recrystallization, column chromatography or the like. (Reference Synthesis Method 3)

The compound represented by the formula (IX) can be produced by reacting the compound represented by the formula (I I I) with a chlorocarbonylating agent.

The reaction is usually performed in a solvent in the presence of a base.

Examples of the solvent used in the reaction include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene, and xylene, hexane, aliphatic hydrocarbons such as' heptane, jetyl ether, Ethers such as lahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, 1,2-jetoxetane, Halogenated hydrocarbons such as roloform, black benzene, dichlorobenzene, nitriles such as acetonitrile, Ν, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazo Examples include aprotic polar solvents such as linone and dimethyl sulfoxide, water, and mixtures thereof.

Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, hydrogenated hydroxide of alkaline metal or alkaline metal such as sodium hydroxide, lithium hydroxide, calcium hydroxide, and the like. Alkali metal such as calcium or alkali earth metal hydride, alkali metal such as sodium carbonate or potassium carbonate, or alkaline earth metal carbonate, sodium ethylate, sodium methylate Examples include organic lithium such as alcoholate, normal butyl lithium, lithium diisopropylamide, and organic bases such as triethylamine, pyridine, and DBU.

Examples of the chlorocarbonylating agent used in the reaction include phosgene, trichloromethyl chloroformate, bis (trichloromethyl) carbonate, and the like. The amount of the reagent used in the reaction is usually 1 to 4 moles of the chlorocarbonylating agent and 1 to 4 moles of the base, based on 1 mole of the compound represented by the formula (I II).

Skin reaction temperature is usually in the range of −78 to 150 ° C., and reaction time is usually in the range of 0.1 to 200 hours.

After completion of the reaction, for example, the compound represented by the formula (IX) is isolated by performing post-treatment operations such as pouring the reaction mixture into water, extracting with an organic solvent, and then drying and concentrating the organic layer. be able to. The isolated compound represented by the formula (IX) can be further purified by column chromatography or the like. After completion of the reaction, the compound represented by the formula (IX) can also be isolated by performing post-treatment operations such as concentrating the reaction mixture as it is. The compound produced by the above synthesis method can be obtained by a method known per se, for example, alkylation, alkenylation, alkynylation, acylation, amination, sulfidation, sulfielation, sulfonation, oxidation, reduction. Substituents can be converted to other desired substituents by halogenation, nitration and the like. As an aspect of this compound, the following are mentioned, for example in this compound. m is 0 or 1 (Ν '— ethyl) benzoylurea compound;

X and Υ are both fluorine atoms (Ν, ethyl) benzoylurea compounds; X and Υ are both chlorine atoms (Ν, ethyl) benzoylurea compounds; X is a fluorine atom and Υ is a chlorine atom Yes (Ν, ェ tyl) benzoylurea compound;

R ¹ is a hydrogen atom (Ν '—ethyl) benzoylurea compound;

R ³ is a C 1 -C 4 alkoxy group optionally substituted with a halogen atom, a halogen atom or a C 1 C 4 alkyl group optionally substituted with a halogen atom (Ν, ethyl) benzoylurea compound ;

R ³ is a halogen atom, a C 1 mono C 4 alkoxy group which may be substituted with a halogen atom, or a C 1 mono C 4 alkyl group which may be substituted with a halogen atom, and m is 0 or 1 ( N, -ethyl) benzoylurea compound;

R ¹ is a hydrogen atom, R ³ is a halogen atom, which may be substituted with a halogen atom, or 1 C 4 alkoxy group or a C 1 -C 4 alkyl group which may be substituted with a halogen atom, (N, -ethyl) benzoylurea compound in which m is 0 or 1. The plant protective agent of this invention contains this compound or its salt, and an inert carrier. Examples of the inactive body include a solid carrier, a liquid carrier, and an ointment base. The plant protection agent of the present invention is usually formulated with an emulsifier, suspending agent, spreading agent, penetrating agent, wetting agent, mucilage agent, stabilizer, etc., if necessary, and formulated into an appropriate form. Yes. Examples of such formulations include emulsions, liquids, microemulsions, emulsions, flowables, oils, wettable powders, aqueous solvents, sols, powders, granules, fine granules, microcapsules, tablets , Ointments, capsules, pellets, poisonous baits, sprays, aerosols, coating agents, etc. In such preparations, the compound or a salt thereof is usually 0.1 to 80% by weight, preferably 1 About 80% by weight is contained. Specifically, when the plant protective agent of the present invention is an emulsion, solution, wettable powder or the like, the present compound or a salt thereof is usually 0.1 to 80% by weight, preferably 10 to When it is contained in an amount of about 80% by weight and is an oil, powder, etc., this compound or a salt thereof is usually contained in an amount of about 0.1 to 50% by weight, preferably about 1 to 20% by weight. In the case of a granule or the like, the present compound or a salt thereof is usually contained in an amount of 0.1 to 50% by weight, preferably about 0.1 to 20% by weight. Examples of solid carriers include vegetable powder (soybean powder, tobacco powder, wheat flour, wood powder, etc.), mineral powder (kaolin, bentonite, acid clay, talc such as talc powder, ore stone powder, etc. And silicas such as diatomaceous earth and mica powder), alumina, sulfur powder, activated carbon, calcium carbonate, ammonium sulfate, sodium bicarbonate, lactose, urea and the like. When a solid carrier is used in the plant protection agent of the present invention, one or more of these solid carriers can be blended at an appropriate ratio. Examples of the liquid carrier include water, alcohols (methyl alcohol, ethyl alcohol, η-propyl alcohol, isopropyl alcohol, ethylene glycol, etc.), ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexane). Hexanone), ethers (tetrahydrofuran, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, etc.), aliphatic hydrocarbons (such as kerosene, fuel oil, machine oil), aromatic hydrocarbons (Toluene, xylene, solvent naphtha, methyl naphthalene, etc.), halogenated hydrocarbons (dichloromethane, black mouth form, tetrachlorocarbon, etc.), acid amides (Ν, Ν-dimethylformamide, Ν, Ν Jimechirua acetamide, Nyu- such methylpyrrolidone), esters (acetate Echiru acetate heptyl, fatty acid glycerol esters, § chromatography Petit-butyrolactone etc.), and, nitriles such (§ Se Tonitoriru, such as propionic nitrile) and the like. When a liquid carrier is used for the plant protection agent of the present invention, one or more of these liquid carriers can be used in combination at an appropriate ratio. Examples of ointment base materials include polyethylene glycol, pectin, polyhydric alcohol esters of higher fatty acids (such as glyceryl monostearate), cellulose derivatives (such as methylcellulose), sodium alginate, bentonite, higher alcohols, many Examples include monohydric alcohols (such as glycerin), petrolatum, white petrolatum, liquid paraffin, lard, various vegetable oils, lanolin, dehydrated lanolin, hardened oil, and resins. When an ointment base is used for the plant protection agent of the present invention, one or more of these soft growth bases can be blended at an appropriate ratio. A surfactant can be further added to the plant protection agent of the present invention as necessary. Examples of the surfactant used in such a case include stalagmites and polyoxins. Siethylene alkyl aryl ethers [e.g., Neugen (trade name) 1-4 2 (EA 1 4 2 (trade name)); manufactured by Daiichi Kogyo Seiyaku Co., Ltd. (non-trade name); Manufactured by Kao Corporation], alkyl sulfates [e.g. Emeral 10 (trade name), emal 40 (trade name); Kao Corporation], alkyl benzene sulfonates [e.g. neogen (trade name), Neogen T (trade name); Daiichi Kogyo Seiyaku Co., Ltd., Neoperex (trade name); Kao Co., Ltd.], polyethylene glycol ethers [For example, Nonipole 8 5 (Product name), Nonipol 1 0 0 (Product) Name), Nonipol 1 6 0

(Trade name); manufactured by Sanyo Chemical Co., Ltd.], polyhydric alcohol esters [for example, Tween 20 (trade name), Tween 80 (trade name); manufactured by Kao Corporation], alkylsulfosuccinates [ For example, Sanmorin 〇 T 2 0 (trade name); Sanyo Chemical Co., Ltd., New Calgen Χ 7 0 (trade name); manufactured by Takemoto Yushi Co., Ltd.], alkyl naphthalene sulfonates, and alkenyl Sulfonates [eg Solpol 5 1 1 5

(Trade name); manufactured by Toho Chemical Co., Ltd.] nonionic and anionic surfactants. In addition to the present compound, the plant protective agent of the present invention includes other insecticides (for example, pyrethroid insecticides, organophosphorus insecticides, carbamate insecticides, neonicotinoid insecticides, natural insecticides). Acaricides, machine oils, nematicides, herbicides, plant hormones, plant growth regulators, fungicides (eg copper fungicides, organochlorine fungicides, organic sulfur fungicides, phenolic fungicides Agent), synergist, attractant, repellent, safener, pigment, fertilizer, etc. may be appropriately blended. Such other insecticides include, for example,

(1) Organophosphorus compounds

Aluminum phosphide, butathiofos, cadusafos, chlorethoxyfos, chlorethoxyfos, chlorpyrifos ^ chlorpyrifos (AP) ), Diazinon,. DCIP (dichlorodi i sopropyl ether), dichlofenthion (ECP), dichlorvos (DDVP), dimethoate, dimethylvinphos, disul foton, EPN, ethion, ethoprophos, etrimfos, Fenthion (MPP), fenitrothion (MEP), fosthiazate, formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, malathion mesulfenfos), methidathion (D TP), monocrotophos, nared (nald: BRP), oxydeprofos (ESP), parathion, phosalone, phosmet: PMP , Pirimiphos-methyl, pyridafenthion> quinalphos, phenthoate: phenthoate: profenofos, propaphos, prothiofos, pyraclorfos, salithion, lith Sulprofos (sul profos), tebupirimfos temephos temephos, tetrachlorvinphos, terbufos, thiometon, trichlorphon (DEP), bamidothion, etc .;

(2) Carbamate compounds

Alanycarb, bendiocarb, benfuracarb, benfuracarb, BPM force carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, ethiofencarb, ethiofencarb, ethiofencarb Fenothiocarb, fenoxycarb, furathiocarb, isoprocarb (MIPC), metolcarb, metomyl, methiocarb, methiocarb, comfort, oxami pirimicarb), propoxur (PHC), XMC, thiodicarb, xylylcarb, etc .;

(3) Synthetic pyrethroid compounds

Acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenhrin, cycloproton (cyclo.prothrin), cyf luthrin, cyhalothrin Cypermethrin, deltamethrin, esfenvalerate, etofenpro, nok Ethofenprox, fenpropathrin, fenvalerate, flucitrate (f lucythrinate), flufenprox, flumethrin, fluvalinate, halfenprox Imiprothrin, permethrin, prallethrin, pyrethrins, resmethrin, sigma-cypermethrin, silafluofen, flu ), Tralomethrin, transfluthrin, 2, 3, 5, 6-tetrafluoro-4- (methoxymethyl) benzyl (EZ) — (1RS, 3RS; 1 RS, 3SR) — 2, 2 —Dimethyl-3-prop 1-enylcyclopropane carbonate, 2, 3, 5, 6-teto Fluoro-4-methylbenzyl (EZ)-(1 RS, 3RS; 1 RS, 3 SR)-2, 2-dimethyl-3-propu-1-enylcyclopropanecarboxylate, 2, 3, 5, 6-tetrafluoro- 4— (Methoxymethyl) benzyl (1RS, 3 RS; IRS, 3 SR) -2, 2—dimethyl 3- (2-methyl-1-monopropenyl) cyclopropanecarboxylate, etc.

(4) Nereistoxin compounds

Car tap, bensul tap, thiocyclam monosultap, bisultap, etc .;

(5) Neonicotinoid compounds

Imidacloprid, tempenram (acetamiprid), acetamiprid, thiamethoxam, thiacloprid, etc .;

(6) Benzylurea compounds

Chlorfluazuron, bistrif luron, difenthiuron, dif lubenzuron, fluazuron, flucycloxuron, flufenoxuron (Flufenoxuron), hexaf lumuron, lufenuron, novaluron, noviflumuron, teflubenzuron triilumuron, etc .; (7) Phenylpyrazole compounds

Acetoprole, fipronil, vaniliprole, pyriprole, pyrafluprole, etc .;

(8) B t toxin insecticide

Live spores and produced crystal toxins from Bacillus thuringiensis, and mixtures thereof;

(9) Hydrazine compounds

Chromafenozide, halofenozide, metho dried sifenozide, tebufenozide, etc .; (10) Organochlorine compounds.

Aldrin, dieldrin, dienochlor, endosulfan, methoxychlor, etc .;

(11) Natural insecticide

Machine oil, nicotine-sulfate;

(12) Other insecticides

Avermectin-B, cyenopyrafen, bromopropylate, buprofezin, chlorphenapyr, chlorphenapyr, cyenopyrafen, cyromazine, ene (1, 3- Dichloroprop) , Emamectin-benzoate, fenazaquin, frepyrazo, flupyrazofos hydroprene, indoxacarb, indoxacarb, lepimectin, metoxadiazone, milbedia Mycin A (milbemycin-A), pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, Flubendiamide, cyilumetofen arsenic acid, benguchiiaz, lime nitrogen (Calciumcyanamide), lime sulfur compound (Calcium polysulf ide), chlordane, DDT, DSP , Flufenerim, phronic amide (nonicamid), flurimfen (flurimfen), formatenate, metham-amnion ium, metham-sodium, odor 匕Methyl bromide, nidinotefuran, potassium oleate, protrifenbute, spiromesifen, sulfur, metaf lumizone, spirote ramama Spir (spirotetramat), pyrifluquinazone (pyrinuquinazon), chlorane traniliprole (Chlorantraniliprole), The following formula (A)

Formula (A)

Inside

R ¹ is Me, C 1, Br or F,

R ² is F, Cl, Br, CI—C 4 haloalkyl, or C 1—C 4 haloalkoxy,

R ³ is F, C 1 or Br,

R ⁴ is H, one or more halogen atoms; CN; SMe; S (O) Me; S (0) ₂ Me and C 1 -C 4 alkyl optionally substituted with OMe, C 3-

C 4 alkenyl, C 3—C 4 alkynyl, C 3—C 5 cycloalkylalkyl, or C 4 1 C 6 cycloalkylalkyl,

R ⁵ is H or Me,

R ⁶ is H, F or C 1,

R ⁷ represents H, F or C 1. ]

And the like. As an active ingredient of an acaricide, for example, Acequinocyl, amitraz, benzoximate, bromopropylate, chinomethionat, chlorobenzilate, CP CB S (chlorfenson), chlorofuente Gin (clofentezine), Kelsen (dicofol), etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, fluproxyfen, fluproxyfen Hexythiazox, propargite (BPPS), polynactins, pyridaben, pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, spirodiclofen Helmet (amidof lumet). Examples of the active ingredient of the nematocide include, for example,

DC IP, fosthiazate, levamisol hydrochloride, methyisothiocyanate, morantel tartarate, imicyafos, etc. The active ingredients of fungicides For example, acibenzolar-S-methyl, ambam, amisulbrom, ampropylfos, anilazine, azoxystrobin, benalaxyl, benalaxyl Nodanil, benomyl, benthiaval icarb, benthiazole, bethoxazin, bitertanol, blasticidin—S (blasticidin-S), pordo 1 Liquid (Bordeaux mixture), Poscalid (boscalid), Bromuconazole Buthiobate, calcium hypochlorite, calcium polysulfide, captan, carbendazol, carboxin, carpropamid, clobbenthiazone , Chloroneb, chloropicrin, chlorothalonil (TPPN), chlorthiophos, cinnamaldehyde, clozylacon, CNA (2, 6-Dichloro- 4- nitroaniline), cupric hydroxide, copper sulfate (Copper) sulfate, cyazofamid, cynuphenamid, cymoxanil, cyproconazole, cyprodinil, cyprofuram, dazomet ゝ debacarb, dike mouth Dic lof luanid, DD (1, 3- Dichlo flower opene), diclosymet, diclomezine, dietofencarb, difenoconazole, diflume tor ira, Dimefluazole (dimef luazole), Dimethirimol (dimethirimol), Dimethomorph, Diniconazole M (.ainiconazole-M) ^ Dinocap (dinocap), Edificenphos (edi fenphos), Enestroburin (enestroburin), Epoxy Epoxiconazole, nickel dimethyl dithiocarbamate, Etaconazole, ethaboxam, et irimol, etridiazole, famoxadone, fenamidone, fenamidone, fenarimol, fenbuconazolam Fendazosulam), fenhexamid, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fenpropamorph, fenthiazone (fenUazon), fent in hydroxide, ferimzone (Ferimzone), fluazinam, fludioxonil, flumetoxonil, flumorph, flumorphimide, fluotrimazole, fluoxastrobin, fluxastrobin Zone one Lumpur (nuQuinconazole), flusilazole (flusilazole), Furusurufuamido (flusulfamide), Furutora;! F lutolanil, fluiriafol fosetyl (fosety 卜 A1), fhalide, fuberidazole; furalaxyl, furametpyr, furcarbanil fluconazole-cis (furconazole) -cis), hexaconazole, hymexazol, I BP (IBP), imazalil, imibenconazole, iminoctadine-albesilate, iminooctadine-albesilate Iminoctadine-triacetate, iodocarb, ipconazole, iprodione, iprovalicarb> isoprothiolane, kasugamycin, cresoki Shim Methyre (kresoxim-methyl), Mancozeb (mancozeb), Mandipropamid (Maneb), Mepanipyrim unepanipyrim, Mepronil, Meptyldinocap, Metalaxyl, Metalaxyl, Metalaxyl metalaxyl-M), metam-sodium, methasulfocarb, methyl bromide, metconazole, methfuroxam, metominostrobin> mezraphenone (metrafenone) Meth-J Rephonox, Mildiomycin, Milneb, Myclobutanil, Microzoline, Nabam, Orysastrobin, Offlace ( ofurace), oxadixyl, oxolinic acid, Oxpoconazole. Oxycarboxin, oxyietracycline pephrazoate (efurazoate penconazole), pencyclon (pencycuron), picoxystrobin, D — ^; —Polycarbin, polyoxin, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb-hydrochloride, Propiconazole (propico), propineb (propineb), broquinazid (proquinazid), prothiocarb, prothioconazole, pyracarlid (pyracarbolid), pyraclostrobin, pyrazophos (pyrazophos) Piributjcarb, pyrifenox Pyrimethanil, pyroquilon, quinoxyfeiu, quintozene (PCNB), silthiophara, simeconazole, sipconazole, sodium hydrogen carbonate (sodium bibarbonate) Sodium hypochlorite, spiroxaraine, SSF— 1 2 9 ((E) -2 [2- (2, 5-dimethylphenoxymethyl) phenyl] -2-methoxyimino-N-ineihylacet amide). Leptomycin, sulfur, tebuconazole, tecloftalam, tetraconazole, thiabendazole, thiadinil, thiram (TMTD), tifluzamide (Thifluzamide), thiophanate-methyl, Torque mouth phos monomethyl (tolclofos-methyl), TPN (TPN), triadimeion (triadimeion), triadimenol, triazoxide, triclamide, tricyclazole, tridemorph (triridemorph), triflumi Triflumizole, trif loxystrobin, triforine, triticonazole, validamycin, vinclozolin, viniconazol, viniconazole, diram (ziram), zoxamide), and herbicide active ingredients and Z or plant growth regulators include, for example, abscisic acid, acetochlor, acifluorfen cif luorfen -sodium), alachlor, alloxydim ^ ametryn Amicarbazone, amidosulfuron, aminoethoxyvinylglycine aminopyralid, AC94, 377, amiprofos-methyl, ancimidos J, ancymidol (asulam), atrazine, aviglycine, azimsulfuron, bef lubutamid, benfluuralin, benfuresate, bensulfuron-methyl, bensuri Bensulide (SAP), bentazone, benthiocarb, benzamizole, benziendizone, benzobicyclon, benzofenap ^ benzyl adenine , Benzylaminopurine (benzylaminopur ine) ^ bialaphos, bifenox, brassinolide, bromacil, bromobutide, bu chlor, butafenacil, butamifos, butyreto (Butylate), caffeenstrole, calcium carbonate, calcium peroxide, carbaryl, chlomethoxynil, Qhloridazon, chlorimron-chlorine ethyl), chlorphthalim, chlorpropham, chlorsulfuron, chlortar 'dimethyl (chlortha 卜 dimethyl), chlorthiamid (DCBN), choline chloride, cinidon-ethyl, cinmethylin, cinosulfuron, clethodim, clomeprop, Cloxyfonac-sodium, chlormequat chloride, 4— CPA (4-ch 1 or ophenoxyace tic acid), cloprop, clofencet, cumyluron, cianazine ( cyanazine), cyclanilide, cyclosulfamuron

(cyclosul.famron), cyhalofop-butyl, 2, 4-dichlorophenoxyacetic acid salts, dichlorprop: 2, 4-DP, daimuron, dalapon. (dalapon: DPA), Jimeten'ami de - P (dimeihenamid-P) _¾ Taminojitto (dami Yuzuru ide, dazomet (dazomet), Teshi alcohol (n-Decyl alcohol) Jikanpa (dicamba- sodium: MDBA), Jikurobe nil (Dichlobenil: DBN), diilufenican, dikegulac, dimethiperate, dimetometry, dimethenamid, diquat, dithiopyr, onion , Endothal, epocholeone, esprocarb, ethephon, ethidimuron, ethoxysulfuron, Ethychlozate, etobenzanid, fenarimol, fenoxaprop-ethyl, fentolazamide, flazasulfuron, flazisulfo, fluasulam -butyl), fluazolate, flucarbazone, flucetosuliuron, flufenacet, flufenpyr, flumetralin, flmnioxazin, flupropane Sodium (flupropanate-sodium), flupirsulfuron-methyl 'sodium (f lupyrsulfuron-methyl-sodium), fluriprimidol (f lui: primidol), full thiaset' methyl (f'luthiacet-methyl), foramsul mouth (foramsul furon) Horkuroruhue! Forchlorfenuron, formesafen, gibberell in, glufosinate, glyphosate, halosulfuron-met yl, hexazinone, imazamox, Imazapic, imazapyr, Imazaquin, imazosulfuron, inabenfide, indole acetic acid (IM), indole butyric acid, iodosulfuron, ioxysulfuron Joxy UoxynU- octanoate , Isouron, isoxachlortole, isoxadifen, karbutilate, lactofen, lenacil, liimron, LGC-42153 (LGC) -42153), maleic hydrazide., Mecoprop (MCPP), MCP salt (MCPA-thioethyl) ), MCPB (2-Methyl-4-chlorop enoxybutanoic acid ethyl ester), mefenacet, mefluidide, mepiquat, mesosulfuron (mesosu) lfuron), mesotrione, methyl daimuron, metolachlor, melibzin, metsulfuron_methyl, molinate, naphthalene acetate naphthylacet ic acid), NAD (1-naphthaleneacetamide), naproanilide, napropamide, n-decyl alcohol, nicosulfuron, n-phenylphthalamic acid, orbencarb (Orbencarb), orthosulfanuron, oxadiazon, oxaziclomefone, oxine-sulfate, paclobutrazol, paraquat ^ Pelargonic acid, pendimethalin, bentoxazone zone), petoxamide, phenmedipham, picloram, picolinafen, pinoxaden, piperonyl butoxide, piperophos , Pretilachlor, primisulfuron-methyl, procarbazone, prodiamine, profluazol, prooxydim, prohexadione-calcium , Prohydrojasmon, promethrin, propain, propoxycarb azone, furyzamide, pyrafruien-ethyl, pyrasulfol (pyrasulfotole) pyrazolate, pyrazosulfuron-ethyl> pyrazoxifene, pyribenzoxim, pyributicarb, pyridafol, pyridate talid), pyriminobac-methyl, pyrithiobac, quiclorac, quinoclamine, quizalofop-ethyl, rimsulfuron, cetoxydim (sethoxydim), siduron, simazine, simetryn, sodium chlorate, sulfosulfuron, swep: MCC, tebuthiuron, tefryltrione (Tefuryltrione), tempotrione (tembotrione), teplaloxy Tepraloxydim, terbacil, terbucarb: terbucarb: MBPMC, thenylchlor, thiazafluron, thidiazuron, thiencarbazone methyl, thifensulfur methyl Triaziflam tribufos> triclopyr, tridiphane, trifloxysulfuron, trifluralin, trinexapac-ethyl, tritosulfuron , Uniconazole- Ρ, Vernalate (PPTC), Fulcetosulfuron, Orthosulianuron, Pinoxaden, Pyrasulfotole, Tefuryltrione ), Examples include tembotrione and thiencarbazone methyl. The active ingredients of synergists include, for example, piperonyl butoxide, sesamex, sulfoxide, N— (2-ethylhexyl) 1, 8, 9, 10-trinorpolone 1 5 Examples of active ingredients in safeners include: -EN-2,3-dicarboximide (MGK 264), WARF-anti-resistant (WARF-anUresistant), and dithy lmaleate. , Benoxacor, cloquintocet-mexyl, ciometrinil, daimuron, dichlormid, fenchlorazole-ethyl, Fenclorim, flurazole (urazole), fluluximen (f luxofenim), furilol (furi l azole), mefenpyr-diethyl, G19 nap thal ic anhydride, oxa betrinyl ( oxabetrini l). In addition to the present compound or a salt thereof, the above-mentioned insecticide, acaricide, machine oil, nematicide, herbicide, plant hormone agent, plant growth regulator, fungicide, synergist , Attractants, repellents, safeners, pigments, fertilizers, etc., the content of these active ingredients in the plant protection agent of the present invention is usually 1 to 80% by weight, preferably 1 About 20% by weight.

Further, the content of the above-mentioned insecticide, herbicide, acaricide and additives other than Z or fungicide in the plant protective agent of the present invention depends on the type and content, or the dosage form of the preparation. Although it is different, it is usually from about 0.000 to 99.9% by weight, preferably about 1 to 99% by weight. More specifically, the surfactant is usually 1 to 20% by weight, preferably about 1 to 15% by weight, the flow aid is about 1 to 20% by weight, and the carrier '(liquid carrier, solid carrier) The ointment base material) is usually about 1 to 90% by weight. More specifically, in the case of a liquid agent, the surfactant is usually contained in an amount of about 1 to 20% by weight, preferably about 1 to 10% by weight, and about 20 to 90% by weight of water. Is preferred. When the plant protective agent of the present invention is an emulsion or a wettable powder (eg, a granular wettable powder), it is usually diluted appropriately with water to a volume ratio of about 10 to 500 times. Used. The plant protection method of the present invention is usually carried out by applying the plant protection agent of the present invention directly to the root or seed of a plant to be protected from pest damage or by applying it to the root zone of the plant.

In the present invention, the plant rhizosphere means the soil and other surrounding parts where the roots are affected. For example, soil in dry fields, paddy fields, upland fields, tea gardens, orchards, seedling cultivation soils and seedlings in seedling boxes, etc. Examples include hydroponic liquids at Matsuto and hydroponic farms. Specific methods for directly applying to roots or seeds include, for example, spraying the plant protection agent of the present invention to roots or seeds, coating, dipping, impregnation, coating, film coating, and pellets. Examples of the coating method include:

As a method of applying to the rhizosphere of a plant, in the case of a hydroponic solution, the plant preservation of the present invention is used. Depending on the state of the rhizosphere of the plant, for example, there is a method of mixing a hydroponic liquid or mixing a hydroponic liquid. For example, soil, seedling culture soil, seedling mats, etc., planting hole treatment (planting hole spraying, planting hole soil mixing), plant source treatment (stock source spraying, plant source soil mixing, plant source irrigation, late seedling season, plant source treatment ), Grooving treatment (spreading grooving, mixing grooving soil), cropping treatment (spreading, sprinkling soil, mixing with soil, sprinkling during growing season), sprinkling treatment at sowing (spreading sprinkling at sowing, sowing) Tokusaku soil mixing), full treatment (full spraying, full soil mixing), other spraying treatments (growth foliar spraying, spraying under canopy or around trunk, soil surface spraying, soil surface blending, sowing hole spraying, buttocks Surface spraying, inter-strain spraying), other irrigation treatments (soil irrigation, seedling irrigation, chemical injection, local irrigation, chemical drip irrigation, chemi-gation), nursery box treatment (nursing box spraying, seedling box irrigation), Seedling tray treatment (spreading seedling tray, irrigating seedling tray) ), Nursery treatment (seedbed spraying, seedbed irrigation, water seedling surrogate seedling spraying, seedling soaking), bed soil admixture treatment (floor soil admixture, floor soil admixture before sowing), and other treatments (culture soil admixing, plowing, topsoil admixture, rain) (Mixed soil in fallen area, planting position treatment, inflorescence spraying, paste fertilizer admixture). The application amount of the present compound or a salt thereof in the plant protection method of the present invention can be appropriately changed according to the application time, application place, application method, formulation form, etc., but when applied to the root zone of a plant, This compound or a salt thereof per hectare is usually about 0.3 to 300 g, preferably about 50 to 300 g, and is applied directly to the root of the plant or palm. In this case, the present compound or a salt thereof is usually from 0.001 to 0.lg, preferably from 0.05 to 0.02 per plant plant or one seed of plant. The ratio is about g. In the plant protection method of the present invention, the application time of the present compound or a salt thereof is expected to be harmful to the target plant by a pest, and when the protection is performed in advance, and depending on the pest to the target plant. It can be selected as appropriate depending on the case where it is carried out for protection after the harm has been confirmed, and is not limited at all. Specifically, for example, fruit vegetables such as eggplant and tomato, cabbage, lettuce, etc. In the case of crops that have undergone the seedling stage such as leafy vegetables, etc. Examples include the growth stage in the field. In addition, in the case of crops that are directly sown in normal fields such as evening sun, corn, and soybean, there are seed stages, seeding stages in the fields, and growth stages. As a method of applying the present compound or a salt thereof to the rhizosphere of a plant, a method of applying the present compound or a salt thereof to soil or the like after the plant root has developed, and applying the present compound or a salt thereof to the soil or the like in advance. And a method for developing plant roots in the soil. The plant protection method of the present invention is generally applied to "crop". Examples of such “crop” include the following “crop”.

"produce"

Corn, rice, wheat, barley, rye, embac, sorghum, cocoon, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, evening baco etc .;

Eggplant vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), cucurbitaceae vegetables (brown cucumbers, capochia, zucchini, watermelons, melons, etc.) Cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, cypress, artichoke yoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus, etc.), celery vegetables (carrot, parsley) , Celery, American Bow Fu, etc.), Zhazaceae Vegetables (Hourenso, Fudansou, etc.), Lamiaceae Vegetables (Perilla, Mint, Basil, etc.), Strawberry, Sweet Potato, Yamanimo, Satoimo, etc .;

^ 卉;

Foliage plant;

Berries (apples, pears, two pears, quince, quince mouth, etc.), berries (peaches, plums, nectarines, ume, sweet potato, apricot, brune etc.), citrus fruits (citrus mandarin orange, orange, lemon, lime, Grapefruit, etc.), nuts (cris, walnuts, hazelnuts, almonds, bisyucho, cashew nuts, macadamia nuts, etc.), berries (bull berries, cranberries, blackberries, raspberries, etc.), grapes, oysters, ori Ibu, bean paste, banana, coffee, date palm, coconut palm, etc .;

Chiya, sardine, flowering tree, roadside tree (ash, birch, dogwood, eucalyptus, ginkgo, lilac, ripe, oak, poplar, hanazo, fu, sycamore, oyster, kurobe, mominoki, tsuga, nezu, pine, Spruce, yew, etc.);

Lawn grass such as Noshipa, Koraishiba, Bermudagrass, Bentgrass, Ryegrass, Bullgrass, Fescue; Pastures such as ryegrass, orchardgrass, fescue, bluegrass, clover, and alfa alpha. The above “crop” includes crops that have been given tolerance to herbicides by classical breeding methods, genetic recombination techniques, and the like. HPPD inhibitors such as Isoxaflutol; ALS inhibitors such as Imagase pills and Thifensulfuron methyl; EPSP synthase inhibitors; Daryumin synthase inhibitors; The use of acetyl CoA carboxyxylase inhibitors; or herbicides such as promoxinil does not cause phytotoxicity problems.

For example, Clearf ie ld® canola with tolerance to imidazolinone herbicides; STS soybeans with tolerance to sulfonylurea herbicides; SR corn that has been given resistance to acetyl acetylase inhibitors. Crop resistance imparted against Asechiru CoA carboxylase inhibitor can be, for example _{p r oc. Nat l. Acad} . Sc i. Is described in USA 1990, 87, 7175 or the like.

Also, a mutant acetyl CoA force lpoxylase that expresses resistance to a acetyl CoA carboxylase inhibitor is known, for example, in Weed Science 53: 728-746, 2005. When a gene that codes for this mutant type of acetyl CoA carboxylase is introduced by genetic recombination technology, or a gene that codes for acetyl CoA carboxylase is introduced with a mutation related to conferring resistance to acetyl CoA carboxylase. In this case, the crop can be conferred with acetyl-CoA-powered lpoxylase-inhibiting herbicide tolerance.

For example, maize varieties that have been given tolerance to glyphosate and dalfosine are known as “crops” that have been given tolerance to herbicides by genetic engineering techniques. Some of these corn varieties are sold under the trade names RoundupReady® and LibertyLink®. The above “crop” also includes crops that have been given the ability to produce insecticidal toxins by genetic engineering techniques.

Such insecticidal toxins include, for example, insecticidal proteins from Bacillus cereus and Bacillus popilie; 6-endotoxins such as CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C from Bacillus thuringiensis, Insecticidal proteins such as VIPK VIP2, VIP3 or VIP3A; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; Protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cis-actin and papain inhibitor; Ribosome inactivating protein (RIP) such as lysine, maize-RIP, abrin, saporin, briodin; 3.—Hydroxysteroid oxidase, ecdysteroid UDP-Darcosyltransferase, steroid metabolism enzymes such as cholesterol oxidase; ecdysone inhibitor; HG-C0A reductase; sodium channel, calcium channel inhibitor, etc. Ion channel inhibitor; juvenile hormone et Cholinesterase; diuretic hormone receptors; stilbene synthase; Biben Gilles synthase; Kichina one peptidase; and Darukanaze the like.

Insecticidal toxins also include eight-ib protein of the insecticidal protein and a protein in which a part of the amino acids constituting the insecticidal protein is deleted or substituted. The hybrid protein is created by combining different domains of the above insecticidal protein by gene recombination technology. As a toxin lacking a part of amino acids constituting the insecticidal protein, for example, CrylAb lacking a part of amino acids is known.

For example, EP-A-0 374 753, TO 93/07278, W0 95/34656, EP-A- 0 427 529, EP-A-451 878, and WO 03/052073.

“Crops” that have been granted the ability to produce insecticidal toxins by genetic engineering techniques are resistant to attack from, for example, Coleoptera, Diptera, Z or Lepidoptera. Among the “crop products” that have been given the ability to produce insecticidal toxins through genetic recombination technology, for example, Yi eldGard® (a corn variety that expresses CrylAb toxin), YieldGard Rootworm® (Cry3Bbl Maize varieties that express toxins), YieldGard Plus® (a corn variety that expresses CrylAb and Cry3Bbl toxins), Herculex I® (phosphinothricin N-acetyltransferase to confer resistance to CrylFa2 toxin and gallofine) (PAT) -expressing corn varieties), UCOTN33B® (CrylAc toxin-expressing evening varieties), Bol lgard I® (CrylAc toxin-expressing evening varieties), Bol lgard II® (CrylAc and Cry2Ab toxins) Express Varieties), VIPCOT® (varietal varieties expressing VIP toxin), NewLeaf® (potato varieties expressing Cry3A toxin), NatureGard® Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Btll Corn polar (CB) traits) and Protecta®. The above “crop” also includes crops that have been given the ability to produce anti-pathogen substances by genetic engineering techniques.

Antipathogenic substances produced by microorganisms include, for example, PR Yunpaku (PRPs, described in EP-A-0392 225); sodium channel inhibitors, calcium channel inhibitors (virus produced KP1, ΚΡ4, ΚΡ6 toxins, etc.) Ion channel inhibitors; stilbene synthase; bibenzyl synthase; chitinase; glucanase;. PR protein; peptide antibiotics, antibiotics with heterocycles; and proteins involved in plant disease resistance ( W0 03/000906)).

Examples of crops that have been given the ability to produce anti-pathogenic substances by genetic engineering techniques are those described in EP-A-0 392 225, W095 / 33818, and EP-A-0 353 191, for example. Can be mentioned. The plant protection method of the present invention can protect plants from harm by pests that cause harm such as feeding or sucking (for example, harmful arthropods such as insects and harmful mites). Specific examples of are as follows.

Hemiptera pests: Laodelphax striatellus, Nilaparvata lugens, Sungats such as Sogatella furcifera, Nephotettix cincticeps, Nephotettix s gossypii), peach aphid (Myzus persicae), radish aphid (Brevicoryne brassicae, churisritsu aphid) (Macrosiphum euphorbiae), potato aphid (Aulacorthum solani), wheat Aphids such as (Toxoptera citricidus), Nezaraantenna, Riptortus clavetus, Leptocorisa chinensis, Eysarcoris parvus, misalta Stink bugs such as Nisshudo plant bug (Lygus lineolaris), on Sit whitefly (Trialeurodes vaporariorum), whiteflies such as bemisia argentifolii, Aonidiella aurantii; Compostaspis perniciosa, Citrus North

(Unaspis citri), Ruby Roe beetle (Ceroplastes rubens), Icerya purchasi, etc. (Cnaphalocrocis medinaUs), Notarcha derogaia> Plodia interpunctella ^ Ostrinia furnacalis, Hellula undalis; pod Sera opt Spodoptera exigua, Pseudaletia separata, Mamestra brassicae, Agrotis ipsilon, Evening managin, Plusia nigrisigna, Trichopulcia, Heliotis, Helicoberpa Such as genus and other species such as Pieris rapae White butterfly, Adkisoff Jesus, Grapholita molesta, Leguminivora glyciiiivorella, Matsumuraeses azukivora, Adoxophyes orana fasciata, Adoxophyes orana fasciata, (Homona magnanima), ^ Darekakumonno ヽ maki (Archips fuscocupreanus), codling moth (Cydia pomonel la), etc .; , Anemone species such as Rionetia, Limantria, Euprotites, etc., Suga such as Plutella xylostella, Pectinophora gossypiella, Jade moth (Phthorimaea operculella), United States Hitori (Hyphantriacunea), Higgaris, Tinea translucens, Koiga (Tineola bisselliella), etc .; Thrips Frozen thrips (Scirtothrips dorsal is), Thrips tabaci, Hirazanazumama (Frankliniella intonsa), Tobacco thrips (Frankliniella fusca) Diptera: Diptera: Musc domestica, Culex popiens pallens, Uban (Tribanus), Hylemya antiqua, Hylemya platura, Anopheles sinensis, Anopheles sinensis Winged fly (Agromyza oryzae), winged winged fly (Hydrellia griseola), winged fly (Chlorops oryzae), edible fly (Dacus cucurbitae), ceratitis capitata, leafworm trifoliate (Liriomyza) Epilachna vigintioctopunctata, Aulacophora femoral is) ^ Phyl lotreta striolata, Oulema oryzae, Echinocneius squameus, Liss trus Callosobruchus chinensis), Shibaosazo Mussel (Sphenophorus venatus), Bean beetle (Popillia japonica), Douganebuoy (Anomal cuprea), Cornroot worm mate (Diabrotica spp.), Colorado worm (Leptinotarsa decemlineata)> serricorne), Anthrenus verbasci, Tribolium castaneum, Lyctus brunneus, Anoplophora malasiaca, Tomicus pinida (Gryllotalpa africana), Oxya yezoensis, Oxya japonica, etc .; Hymenoptera: Athalia rosae, Acromyrmex spp., Fuyaant (Solenopsis spp.), Etc. : Rice Singale Sentiyu (Aphelenchoides besseyi), Ichi Mesenchu © (Nothotylenchus acris), etc.; Blattodea pests: Chiya panel cockroach (Blattella gerinanica), fuliginosa (Periplaneta fuliginosa) ^ ヮ Mon cockroach (Periplaneta americana), 卜 bee mouth cockroach (Periplaneta brunnea), eastern cockroach (Blatta orientalis), etc .; Nigeria, Aculopspelekassi, etc. Fushida II, Polyphagotarsonemus latus, etc., Nigeria, Nigeria, Tyrophagus putrescentiae, M. ) 、

(Deriatophagoides ptrenyssnus) and other ticks, Cheletus eruditus, Cheletus malaccensis, Southern mite

Ticks such as (Cheyletus moorei). Next, although a synthesis example, a formulation example, a test example, etc. are given and this invention is demonstrated further in detail, this invention is not limited to these. First, the synthesis example of this compound is shown.

Synthesis example 1

4-Chloro-N-ethylaniline 1.01 g in a solution of 4.0 ml of jetyl ether

A solution prepared by dissolving 1.18 g in 1.0 ml of diethyl ether was added under ice-cooling, and the mixture was stirred at room temperature for 2 hours. Hexane 5m 1 is added to the reaction mixture, followed by filtration, and the filtrate is dried to give 3- (4 monochlorophenyl) —1— (2, 6-difluoro oral benzoyl) 1 3 1 ethyl Urea (hereinafter referred to as the present compound (1)) 2. 13 g was obtained.

This compound (1)

— NMR (DMSO— d ₆ ) δ (p pm): 1. 01 (3H, t), 3. 65 H, q), 7. 12-7. 16 (2H, m), 7. 25— 7. 27 (2H, m), 48 -7. 50 (3H, m), 10. 50 (1 H, br s) Synthesis example 2

4-Chromium 1-N-ethylaniline 1. In a solution of 01 g dissolved in Jetyl ether 4.0 ml, 2-Fluoro 4-Chronobenzene benzoyl isocyanate 1. 28 in Jetyl ether 1.0 ml The solution dissolved in was added under ice cooling and stirred at room temperature for 2 hours. After adding 2.5 ml of hexane to the reaction mixture, filtering, and drying the filtrate, 1 1 (2-chloro-6-fluobenzoyl) 1 3- (4-chlorophenyl) 1 3— Ethylurea (hereinafter referred to as the present compound (2)) 1. 90 g was obtained.

This compound (2)

^X H-NMR (DMS 0 1 d ₆ ) <5 (p pm): 1. 00 (3H, t), 3. 65 (2 H, q), 7. 26-7. 29 (3 H, m) , 7. 32- 7. 34 (1 H, m), 7. 43-7. 50 (3H, m), 1.0. 49 (1H, brs) Synthesis Example 3

4-Dichloro N-ethyl aniline 1. In a solution of 01 g dissolved in 4.0 ml of jetyl ether, 1. 39 g of 2,6-dichlorobenzoic isocyanate 1.39 g of Jetyl ether 1.0 ml The solution dissolved in was added under ice cooling and stirred at room temperature for 2 hours. Add 5m 1 of hexane to the reaction mixture, filter, and dry the filtrate to give 3- (4-chlorophenyl) 1- (2,6-dichlorobenzoyl) 1 3-eth Luurea (hereinafter referred to as the present compound (3)) 2. 14 g was obtained.

This compound (3)

^ -NMR (DMSO-d ₆ ) δ (p pm): 0.99 (3H, brs), 3

3 (2H, b rs), 7. 27- 7. 28 (2H, m), 7. 39 (1H, m),

41-7. 47 (4H, m), 10. 45 (1 H, brs) Synthesis example 4

N-ethyl-1-fluoro-4- (1, 1, 2, 2-tetrafluoroethoxy) aniline 0.51 g in a solution of 2.0 ml of jetyl ether in a solution of 2,6-difluorobenzo A solution prepared by dissolving 0.36 g of ylisocyanate in 0.5 ml of jetyl ether was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. Hexane 5m 1 is added to the reaction mixture, followed by filtration. The filtrate is dried to give 1- (2,6-difluorobenzoyl) 1 3-ethyl-3- [2-fluoro-4- (1, 1, 2 , 2-tetrafluoroethoxy) phenyl] urea (hereinafter referred to as the present compound (4)) 0.75 g was obtained.

This compound (4)

tH— NMR (DMSO-d ₆ ) δ (p pm): 1.03 (3H, t), 3.62 (2 H, q), 6. 70-6. 96 (1 H, m), 7. 10-7. 15 (2H, m), 7.21-7.23 (1 H, m), 7. 37-7.40 (1 H, m), 7. 45-7.52 (2H, m ), 10. 71 (1H, brs) Synthesis Example 5

N-Ethyl-2-Fluoro-4 (1, 1, 2, 2-Tetrafluoroethoxy) aniline 0.5- 2 In a solution of 1 g dissolved in jetyl ether 2.0 ml, 2-chloro 6-full A solution prepared by dissolving 0.39 g of o-benzoyl isocyanate in 0.5 ml of jetyl ether was added under ice-cooling, and the mixture was stirred at room temperature for 2 hours. After adding 10 ml of hexane to the reaction mixture, the mixture is filtered, and the filtrate is dried to obtain 1 1 (2-chloro 6-fluorobenzoyl) 1 3-ethyl-3- 3 [2-fluoro- 4 1 (Tetrafluoroethoxy) phenyl] Urea (hereinafter referred to as the present compound (5)) 0.79 g was obtained.

This compound (5)

^ -NMR (DMSO-d ₆ ) δ (p pm): 1. 03 (3H, t), 3.62 H, q), 6. 70-6. 96 (1 H, m), 7. 21— 7. 28 (2H, m), 31-7. 33 (1H, m), 7. 37-7. 51 (3H, m), 10. 72 H, brs) Synthesis example 6

N-Ethyl-2-fluoro-4- (1,1,2,2-Tetrafluoroethoxy) aniline 0.51 g in a solution of 2.0 ml of jetyl ether in a solution of 2,6-dichlorobenzo A solution prepared by dissolving 0.42 g of ylisocyanate in 0.5 ml of jetyl ether was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. Add 5 ml of hexane to the reaction mixture, filter, and dry the filtrate to obtain 1 1 (2,6-dichlorobenzoyl) 1 3 -ethyl 3-[2 -fluoro 4 1 (tetrafluoro 4 C) Phenyl] Urea (hereinafter referred to as the present compound (6)) 0.8 lg was obtained.

This compound (6)

— NMR (DMSO-d ₆ ) δ (p pm): 1. 04 (3H, t), 3. 63 H, q), 6. 58— 6. 85 (1 H, m), 7. 16— 7 19 (1H, m), 25- 7.28 (1H, m), 7. 34-7. 48 (4H, m), 10. 37 H, brs) Synthesis Example 7

N-Ethyl-2-fluoro-4- (trifluoromethyl) aniline 0.51 g in jetyl ether 2. OmU dissolved solution, 2,6-difluorobenzoyl isocyanate 0.44 g in jetyl ether The solution dissolved in 0.5 ml was added under ice-cooling and stirred at room temperature for 2 hours. Add 5 ml of hexane to the reaction mixture 1- (2, 6-Difluorobenzoyl)-3-ethyl-3-[2-Fluoro-4 (trifluoromethyl) phenyl] urea by filtering and drying the filtrate

(Hereinafter referred to as the present compound (7).) 0.73 g was obtained.

This compound (7)

^X H-NMR (DMSO-d ₆ ) δ (ppm): 1. 04 (3H, t), 3. 67 H, q), 7. 11-7. 16 (2H, m), 7. 48— 7 52 (1H, m), 61-7. 66 (2H, m), 7.82—7.85 (1H, m), 10. 80 H, brs) Synthesis Example 8

2-Chloro-6-fluorobenzoyl isocyanate 0.48 in a solution of 0.51 g of N-ethyl-2-fluoro-4 aniline (trifluoromethyl) aniline in 2.0 ml of jetyl ether A solution in which 0.5 g of g was dissolved in 0.5 ml of Jetiljetel was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. Add 10 ml of hexane to the reaction mixture, filter from T, and dry the filtrate. 1 1 (2-Chloro-6-fluorobenzoyl) —3-Ethyl 3— [2-Fluoro-4 1 (Trifluoromethyl) ) Phenyl] Urea (hereinafter referred to as the present compound (8)) 0.73 g was obtained.

This compound (8)

^X H-NMR (DMSO— d ₆ ) δ (p pm): 1. 04 (3Η, t), 3. 67 (2H, q), 7. 24-7. 34 (2H, m), 7. 42 -7. 48 (1 H, m) '7. 62-7. 68 (2H, m), 7. 82-7. 85 (1 H, m), 10. 80 (1H, brs) Synthesis Example 9 N-ethyl-2-fluoro-4- (trifluoromethyl) aniline 0.51 g in a solution of 2.0 ml of jetyl ether in a solution of 2,6-dichlorobenzoyl isocyanate 0.52 g of jetyl ether 0 A solution dissolved in 5 ml was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. Add 5 ml of hexane to the reaction mixture, filter, and dry the filtrate to obtain 1- (2, 6-dichlorodibenzoyl) —3—Ezirou 3— [2-Fluoro-4 (Trifluoro) (Methyl) phenyl] urea (hereinafter referred to as the present compound (9)) 0.79 g was obtained.

This compound. (9)

^ -NMR (DMSO— d ₆ ) δ (p pm): 1. 06 (3H, t), 3.68 (2 H, q), 7. 36-7. 42 (3H, m), 7. 59 — 7. 61 (2H, m), 7. 69-7. 72 (1H, m), 10. 48 (1H, brs) Production Example 10

1— (2,6-Difluorobenzoyl) 1 3— [2-Fluoro-4 1 (trifluoromethyl) phenyl] —3-Ethylurea 0.90 g of 1-methyl-2-pyrrolidone 9.0 ml 11 lmg of sodium hydride was added to the solution dissolved in and stirred at 2 ° C for 30 minutes. To the mixture was added 0.335 ml of methyl iodide and stirred at 2-3 for 4 hours. A mixture of 9 ml of saturated aqueous ammonium chloride and 9 ml of water was added to the reaction mixture under ice cooling, and the mixture was extracted 3 times with 20 ml of ethyl acetate. The organic layers were combined, washed with saturated brine three times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate: chloroform: hexane = 1: 1: 4) to give 1— (2,6-difluobenzoyl) 1-3-ethyl-3— [2-Fluoro-4 mono (trifluoromethyl) phenyl] 1 1 monomethylurea (hereinafter referred to as the present compound (10)) 0.79 g was obtained.

Compound of the present invention (10)

^X H-NMR (DMSO-d ₆ , 80 ° C) δ (p pm): 1. 06— 1. 1 0 (3 H, t, J = 7.1 Hz), 3.01 (3H, s), 3. 68— 3. 74 (2H, q, J = 7.1 Hz), 7. 08-7. 12 (2H, m), 7. 44— 7. 60 (3 H, m), 7. 71- 7. 74 (1H, m) Production Example 1 1

1- (2-Chrome mouth 6-Fluorobenzoyl)-3-[2-Fluoro-4-1 (Trifluoromethyl) phenyl] 1 3-Ethylurea 1. 01 g of 1-Methyl-2-one Pyrrolidone 10 To the solution dissolved in 0 ml, 18 mg of sodium hydride 1 was added and stirred at 2 for 30 minutes. To the mixture was added 0.37 ml of methyl iodide, and the mixture was stirred at 2-3 ° C for 3 hours. A mixture of saturated aqueous ammonium chloride solution 1 Om 1 and water 1 Om 1 was added to the reaction mixture under ice-cooling, and the mixture was extracted 3 times with ethyl acetate 2 Om 1. The organic layers were combined, washed 3 times with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate: black mouth form: hexane = 1: 1: 4) to give 1 (2-chloro-6-fluorobenzoyl) -3-ethyl- 3— [2-Fluoro-4 mono (trifluoromethyl) phenyl] 1 1 1 methylurea (hereinafter referred to as the present compound (1 1)) 0.84 g was obtained.

Compound of the present invention (1 1)

^ -NMR (DMSO-in _{d 6, 80) 6 (p} pm):. 1. 09- 1. 12 (3 H, m), 2. 94 (3H, brs), 3. 74-3 76 (2H M), 7.20 -7. 25 (1H, m), 7.30-7.32 (1H, m), 7.33—7.50 (1H, m), 7.58—7.62 (2H, m), 7.72—7.75 (1 H, m) Production Example 12

1— (2,6-Dichlorobenzol) 1-3— [2-Fluoro4-1 (trifluoromethyl) phenyl] —3—Ethylurea 1.01 g of 1-methyl-2-pyrrolidone in a solution of 10.0 ml Sodium hydride 1 1 3 mg was added and stirred at 2 for 30 minutes. To the mixture was added 0.335 ml of methyl iodide and stirred at 2-3 ° C for 4 hours. A mixture of 10 ml of saturated aqueous ammonium chloride and 10 ml of water was added to the reaction mixture under ice cooling, and the mixture was extracted 3 times with 2 Oml of ethyl acetate. The organic layers were combined, washed three times with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate: black mouth form: hexane = 1: 1: 4) to give 1- (2,6-dichlorobenzoyl) —3—ethyl-3— [2 —Fluoro-4- (trifluoromethyl) phenyl] 1. 1-methylurea (hereinafter referred to as the present compound (12)) 0.78 g was obtained. Compound of the present invention (12)

^ -NMR (DMSO— d ₆ , 80. C) δ (p pro): 1. 14— 1. 18 (3 H, m), 2. 85 (3H, brs), 3. 78— 3. 80 ( 2H, m), 7. 39 — 7.46 (3H, m), 7. 6 1 -7. 63 (1H, m), 7. 74-7. 76 (2H, m) Production Example 13

1 1 (4 1-phenyl) 1 3- (2, 6-difluorobenzoyl)-1-ethyl urea 1. 1 g of 1-methyl-2-pyrrolidone dissolved in 10.0 ml Then, 142 mg of sodium hydride was added and stirred at 2 for 30 minutes. To the mixture, 0.44 ml of methyl iodide was added, and the mixture was stirred at 2-3 ° C for 3 hours. A mixture of 10 ml of saturated ammonium chloride aqueous solution and 10 ml of water was added to the reaction mixture under ice cooling, and the mixture was extracted 3 times with 2 Oml of ethyl acetate. The organic layers were combined, washed three times with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel force chromatography (ethyl acetate: black mouth form: hexane = 1: 1: 4) to give 1 1 (4 1 black mouth phenyl) 1 3— (2, 6-difluor). Lobenzoyl) 1-ethyl 3-methylurea (hereinafter referred to as the present compound (13)) g was obtained.

Compound of the present invention (13)

_{^ -NMR (DMSO- d 6, 80} ^) δ (p pm): 1. 00 - 1. 04 (. 3 H, t, J = 7 1Hz), 2. 91 (3H, s), 3. 63 -3.68 (2H, q, J = 7 lHz), 7. 08-7. 16 (4H, m), 7. 42-7. 45 (2 H, m), 7. 47 -7. 55 (1H, m) Production Example 14

1 1 (2-Chloro 6-Fluorobenzoyl) —3— (4-Chlorophenyl) 1 3-Ethylurea 1. Hydrogenated into a solution of 10.0 g of 1-methyl-2-pyrrolidone in 10.0 ml Sodium 35 mg was added and stirred at 2 ° C for 30 minutes. To the mixture, 0.42 ml of methyl iodide was added and stirred at 2-3 ° C for 3 hours. To the reaction mixture was added a mixture of saturated ammonium chloride aqueous solution 10 ml 1 and water 10 ml 1 under ice-cooling, and the mixture was extracted 3 times with 2 ml of ethyl acetate. The organic layers were combined, washed with saturated brine three times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to Siri-force gel column chromatography (ethyl acetate: black mouth form: hexane = 1: 1: 1) to give 1 1 (2-chloro-6-fluorobenzoyl) 1 3— ( 4-Chlorophenyl) 1-3-ethyl-1-methylurea (hereinafter referred to as the present compound (14)) 1.02 g was obtained.

Compound of the present invention (14)

^X H-NMR (DMS〇1d ₆ , 80) δ (p pm): 1. 04— 1. 07 (3 H, t J = 7.0 Hz), 2. 86 (3H, s), 3. 66 -3. 71 (2H, q, J = 7.0 Hz 7. 20 -7. 32 (4H, m 7. 43-7. 49 (3 H, m) Production Example 15

1— (4—Black mouth phenyl) —3— (2, 6—Dichloro mouth benzoyl) — 1-methyl urea 1.01 g in 1-methyl-2-pyrrolidone solution in 10.0 ml sodium hydride 129 mg And stirred at 2 ° C for 30 minutes. To the mixture was added 0.40 ml of methyl oxalate and stirred at 2-3 for 3 hours. To the reaction mixture, a mixture of 10 ml of saturated aqueous ammonium chloride and 10 ml of water was added under ice cooling, and the mixture was extracted 3 times with 2 ml of ethyl acetate. The organic layers were combined, washed with saturated brine three times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate: black mouth form: hexane = 1: 1: 4), and 1 (4—black mouth phenyl) —3— (2, 6-dichlorobenzene). 1) -Ethyl-3-methylurea (hereinafter referred to as the present compound 15). 0. 84 g was obtained.

Compound of the present invention (15)

^ -NMR (DMSO— d ₆ , 80 ° C) δ (ρ pm): 1. 11— 1. 13 (3 Η, br), 2. 80 (3 Η, br s), 3. 72— 3. 76 (2H, br), 7. 35-7. 46 (7H, m) Production Example 16

1-(2, 6-Difluorobenzoyl) —3— [2-Fluoro-4 (1, 1, 2, 2-tetrafluoromethoxy) phenyl] 1 3-Ethylurea —Methyl-2-pyrrolidone 9. To a solution dissolved in Oml, 10 Omg of sodium hydride was added and stirred at 2 ^ for 30 minutes. To the mixture was added methyl iodide 0.31 ml and stirred at 2-3 for 3 hours. A mixture of 9 ml of saturated aqueous ammonium chloride and 9 ml of water was added to the reaction mixture under ice-cooling, and the mixture was extracted 3 times with 20 ml of ethyl acetate. The organic layers were combined, washed with saturated brine three times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (vinegar Acid: Ethyl chloride: Chloroform: Hexane = 1: 1: 4), 1 1 (2, 6-difluoro-benzoyl) 1 3-ethyl 3--3 [2-Fluoro 4 1 (1, 1 , 2,2-tetrafluoromethoxy) phenyl] 1-methylurea (hereinafter referred to as the present compound (16)) 0.85 g was obtained.

Compound of the present invention (16)

^X H-NMR (DMSO-d ₆ , 80. C) δ (ρ pm): 1. 05— 1. 09 (3 Η, t, J = 7.1 Hz), 2. 98 (3H, s), 3 64— 3. 70 (2H, q, J == 7.2 Hz), 6. 58— 6. 85 (1 H, m), 7. 07-7. 17 (3 H, m), 7. 28 -7. 35 (2H, m), 7. 48-7. 56 (1H, m) Production Example 17

1 (2—Black mouth—6-Fluoro mouth Benzoyl) 1 3— [2-Fluoro—4 1 (1, 1, 2, 2-Tetrafluoromethoxy) phenyl] —3-Ethylurea 0.91 To a solution of g in 1-methyl-2_pyrrolidone 9. lm 1, 96 mg of sodium hydride was added and stirred at 2 ° C for 30 minutes. To the mixture was added methyl iodide 0.30 ml and stirred at 2-3 for 3 hours. A mixture of saturated ammonium chloride aqueous solution 9m 1 and water 9m 1 was added to the reaction mixture under ice-cooling, and the mixture was extracted 3 times with ethyl acetate 20m 1. The organic layers were combined, washed 3 times with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate: black mouth form: hexane = 1: 1: 4) to give 1- (2-black mouth—6-fluorobenzoyl) —3 —Ethyl 3— [2-fluoro-4- (1, 1, 2, 2-tetrafluoromethoxy) phenyl] 1 1 1-methylurea (hereinafter referred to as the present compound (17)) 0.78 g Obtained.

Compound of the present invention (17)

_{iH- NMR (DMSO- d 6, 80} ° C) δ (p pm): 1. 08- 1. 1 1 (. 3 H, t, J = 7 0Hz), 2. 92 (3H, s), 3 69-3. 73 (2H, q, J = 7.0 Hz), 6. 58-6. 86 (1H, m), 7. 16-7. 24 (2 H, m), 7. 29-7 32 (2H, m), 7. 44- 7.49 (2H, m) Production Example 18

1-(2, 6-Diclonal Benzoyl)-3-[2-Fluoro-4- (1, 1, 2, 2-tetrafluoromethoxy) phenyl] 1 3-Ethylurea 1. 0 1 g 1 -Methyl-2-pyrrolidone 10. To a solution dissolved in Oml, 102 mg of sodium hydride was added and stirred at 2 ° C for 30 minutes. To the mixture was added 0.332 ml of methyl iodide, and the mixture was stirred at 2-3 ° C for 4 hours. To the reaction mixture was added a mixture of saturated aqueous sodium chloride 1 Om 1 and water 1 Om 1 under ice-cooling, and the mixture was extracted 3 times with ethyl acetate 2 Om 1. The organic layers were combined, washed 3 times with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate: chloroform: hexane = 1: 1: 4) to give 1— (2,6-dichlorobenzene) 1-3-ethyl-3- [2 —Fluoro-4-1- (1,1,2,2-tetrafluoromethoxy) phenyl] 1-11-methylurea (hereinafter referred to as the present compound (18)) 0.84 g was obtained.

The present compound (18)

^X H-NMR (DMSO— d ₆ , 8 OV) δ (p pm): 1. 1 1-1. 14 (3 H, br), 2. 83 (3H, brs), 3. 74— 3. 77 (2H, br), 6. 59-6. 87 (1H, m), 7. 17— 7. 20 (lH, m), 7. 30— 7. 32 (1H, m), 7. 42-7 45 (3H, m), 7. 56-7. 6 1 (1 H,

Next, formulation examples are shown. In addition, a part represents a weight part.

Formulation Example 1

10 parts of this compound (1) to (9), 35 parts of xylene and N, N-dimethylform Dissolve in a mixture with 35 parts of amide, add 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mix well to obtain 10% emulsions. Formulation Example 2

Add 20 parts of this compound (1) to (9) to a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth and mix well. To obtain each 20% wettable powder. Formulation Example 3

Add 1 part of synthetic silicon hydroxide-containing fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay to 2 parts of this compound (1) to (9) and mix thoroughly. Next, an appropriate amount of water is added to these mixtures, further stirred, granulated with a granulator, and dried by ventilation to obtain 2% granules. Formulation Example 4

Dissolve 1 part of this compound (1) to (9) in an appropriate amount of acetone, add 5 parts of synthetic hydrous silicon oxide fine powder, 0.3 part of PAP and 93.7 parts of Fusasa Mikule, and mix well with stirring. Acetone is removed by evaporation to obtain each 1% powder. Formulation Example 5

This compound (1) to (9) 10 parts; 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt; and 55 parts of water are mixed together and finely powdered by wet powdering. Get each 10% flowable. Formulation Example 6

This compound (1)-(9) 0.1 part is melt | dissolved in 5 parts xylene and 5 parts trichloroethane, this is mixed with 89.9 parts of deodorizing kerosene, and each 0.1% oil agent is obtained. Formulation example Ί

10 mg of this compound (1) to (9) is dissolved in 0.5 ml of acetone, and this solution is mixed with animal solid feed powder (solid feed powder CE-2 for breeding, Nippon Claire Co., Ltd. Product) Process to 5 g and mix evenly. Acetone is then evaporated to dryness to obtain each poisonous bait. Next, test examples show that the plant protection method of the present invention is useful.

Test example 1

This compound (1), (2), (4), (5), (7), (8), (9), (10) (11), (13), (14), (16) and ( 17) 5mg each of Sorgen TW-20 (Daiichi Kogyo Seiyaku Co., Ltd.) and acetone mixed solution (mixing volume ratio; Sorgen TW-20: Acetone = 1: 19) dissolved in 0.1ml, 3m 1 with ion-exchanged water A test chemical solution for the test compound was prepared by diluting the test compound. Cabbage seedlings were grown in a seedling container (capacity: 27 ml, height: 5. O cm) to 2.5 leaf stage. The whole amount of the test solution was irrigated on the surface of the cabbage seedling. 5 days after the treatment, the roots of cabbage seedlings were removed, the stems and leaves were placed in a polyethylene cup (capacity 18 Oml), and the first instar larvae of Spodoptera litura were released and stored at 25 ° C for an additional 7 days. . Then, the cabbage seedlings were examined for the degree of damage caused by Lotus moth larvae, compared with the case where the test compound was treated (treated area) and the case where it was not treated (untreated area). The damage control effect was sought. The degree of food damage in the treatment area

Damage control effect (%) X 100

Degree of damage in untreated areas

As a result, this compound (1), (2), (4), (5), (7), (8), (9), (10) (1 1), (13), (14), ( In the treatment areas of 16) and (17), the damage control effect was 90% or more, and the cabbage seedlings could be protected from the damage caused by Spodoptera litura. Test example 2

This compound (4), (5), (7), (8), (10), (11), (16) and (17) 5 mg each of Sorgen TW-20 (Daiichi Kogyo Seiyaku) Mixed solution (mixed volume ratio; Sorgen TW-20: Acetone = 1: 19) Dissolved in 0.1 ml, diluted to 3 ml with ion-exchanged water, prepared a test drug solution for the test compound. A seedling container (capacity: 27 ml, height: 5.0 cm) was filled with soil and sown with cabbage. The whole amount of the test chemical was irrigated on the soil surface. The cabbage was raised until 28 days after the treatment. This key The roots of the seedlings were removed, the foliage was placed in a polyethylene cup (capacity 180 ml), and 10 second-instar larvae of Plutellaxylostella were released and stored at 25 ° C for an additional 7 days. The cabbage seedlings were then examined for the degree of damage caused by the diamondback larvae, comparing the case where the test compound was treated (treated area) and the case where it was not treated (untreated area). Asked. The degree of food damage in the treatment area

Damage suppression effect (%) = 1 X 100

\ Degree of damage in the untreated area No. As a result, in the treated area of this compound (4), (5), (7), (8), (10), (11), (16) and (17) Showed a damage control effect of over 90%, and was able to protect cabbage seedlings from the damage caused by the diamondback moth.

Claims

54

Formula (I)

[Where.

X and Y each represents a fluorine atom or a chlorine atom,

R ¹ is a hydrogen atom, a C 1 -C 6 alkyl group which may be substituted with a halogen atom, a C 2 -C 6 alkenyl group which may be substituted with a halogen atom, a C 2 -C 6 alkynyl group, C6—C14 aralkyl group, C7—C11 aralkyl group, C2—C6 alkoxyalkyl group, C7—C14 aralkyloxyalkyl group, C3—C6N, N-di (alkyl) aminoalkyl group, C2 -C6 alkylthioalkyl group, C2-C6 alkylsulfinylalkyl group, C2-C6 alkylsulfonylalkyl group, C3-C9 alkoxyalkoxyalkyl group, C2-C6 alkoxycarbonyl group, C8- C 12 aralkyloxycarbonyl group, N, N—di (C 1 C 6 alkyl) force rubamoyl group, C 2—C 6 alkylcarbonyl group optionally substituted with halogen atom, formyl group, halogen atom C 1 -C 5 It represents alkylsulfonyl group or a C 6- C 10 § Li one Rusuruhoniru group, R ² represents a halogen atom or a halogen atom which may be substituted C 1-C 4 alkyl group,

R ³ is a C 1 -C 4 alkyl group which may be substituted with a halogen atom, a hydrogen atom or a rogen atom, a C 1 -C 4 alkoxy group which may be substituted with a halogen atom, or a C atom which is optionally substituted with a halogen atom A 2-C6 alkoxyalkoxy group, a C2-C4 alkenyloxy group optionally substituted with a halogen atom or a C2-C4 alkynyloxy group optionally substituted with a halogen atom;

m represents an integer of 0 to 4. ]

(Ν'-ethyl) A method for protecting a plant from damage by pests, which comprises applying an effective amount of a benzoylurea compound or a salt thereof to the root or seed of a plant or the rhizosphere of a plant.

2. In formula (I), R ¹ is a hydrogen atom, R ³ is a halogen atom, a C 1 -C 4 alkoxy group that may be substituted with a halogen atom, or a C atom that is optionally substituted with a halogen atom Claims having a step of applying an effective amount of a benzoylurea compound or a salt thereof, which is a 1-C4 alkyl group and m is 0 or 1 to the root or seed of a plant, or the rhizosphere of a plant Item 1. A method for protecting plants from harm by pests according to item 1.

3. The plant protection method according to claim 1, wherein the root or seed of the plant or the root zone of the plant is the root zone of the plant.

4. The plant protection method according to claim 3, wherein the rhizosphere of the plant is soil on which the plant grows.

5. Formula (I)

[Where,

X and Υ each represent a fluorine atom or a chlorine atom,

R ¹ is a hydrogen atom, a C 1 C 6 alkyl group optionally substituted by a halogen atom, a C 2 -C 6 alkenyl group optionally substituted by a halogen atom, a C 2 -C 6 alkynyl group, C6—C 14 aryl group, C 7—C 11 aralkyl group, C2—C6 alkoxyalkyl group, C 7—C 14 aryloxyalkyl group, C3—C6N, N—di (alkyl) aminoalkyl group, C 2 — C 6 alkylthioalkyl group, C2-C 6 alkylsulfinylalkyl group, C 2— C 6 alkylsulfonyl alkyl group, C 3— C 9 alkoxyalkoxyalkyl group, C 2—C 6 alkoxycarbonyl group, C 8— C 12 aralkyloxycarbonyl group, N, N-di (CI—C 6 alkyl) force rubamoyl group, optionally substituted with halogen atom C 2—C 6 alkylcarbonyl group, formyl group, halogen atom C optionally substituted 1 -C 5 alkyl sulfonyl group, or a C 6- C 10 § Li one Rusuruhoniru group, R ² represents a halogen atom or may be substituted by a halogen atom C 1-C4 alkyl group, 56

R ³ is a halogen atom, an optionally substituted C 1—C4 alkyl group, an optionally substituted C 1—C4 alkoxy group, an optionally substituted C 2— A C6-alkoxyalkoxy group, a C2-C4 alkenyloxy group optionally substituted with a halogen atom or a C2-C4 alkynyloxy group optionally substituted with a halogen atom,

m represents one of integers from 0 to 4. ]

(Ν'-ethyl) A plant protecting agent from harmful organisms containing a benzoylurea compound or a salt thereof and an inert carrier.

6. In formula (I), R ¹ is a hydrogen atom, R ³ is a halogen atom, a C 1 -C 4 alkoxy group that may be substituted with a halogen atom, or a C 1 that is optionally substituted with a halogen atom A plant protecting agent from harmful organisms according to claim 5, which is a C4 alkyl group and m is 0 or 1 (Ν'-ethyl) benzoylurea compound or a salt thereof and an inert carrier. .

7. The plant protective agent according to claim 5, which is used for treatment of a plant into the rhizosphere.

8. The plant protective agent according to claim 5, which is used for treating soil in which plants grow.

9. (Ν '-ethyl) benzoyl urea compound or its salt for application to plant root or seed or plant rhizosphere to protect plant from harm by pests Use of.